The most awkward sex stories from guys who lived to tell

(Illustration by Jekun/ Very Good Light)

Awkward sex makes for juicy (or cringe-worthy, you tell us!) stories.

We asked Very Good Light’s own Lighters on Instagram to send in their most daring experiences – ones that they lived to tell! From a story about a host family, to one involving a boss’ desk, to another involving someone’s mother – ya’ll, brace yourselves. Sex: sometimes it’s really freaking funny.

The Office

I’ve always had fantasies of having sex in someone’s office. I just didn’t know it’d be so awkward.

I met this guy who invited me on a weekend to come meet with him at his office. We met on the ground floor and he took us up to his workplace. Inside were dozens of cubicles and it seemed like a standard place of work. I asked where his office was, which is when he admitted that he actually didn’t have an office – we’d be having sex in his boss’s office.

While in theory that could be hot, I realized it wasn’t cool when we were on his desk, exchanging slobber all over his floor and bodily fluid. He was so cool and casual about it and all I could think about is how pissed I’d be if I found dried splooge on my desk Monday morning.

The Host (Family)

A few years ago, I met up with this Mexican exchange student who lived in this really big house. He told me to come over and before I did, I asked if he was alone. He assured me it would be all fine and that I was in the clear to come over.

We ended up sneaking into this office, where I realized there were photos of his host family. They looked super kind and really sweet. I felt really weird having sex while all the lights were on, their photos staring back at me.

The sex was okay and it was fun until I heard a crowd of people walking through the door.

“Who’s that?!” I asked, super paranoid.

“Oh, just my host family.”

“Do they know I’m here?”

“No, but it’s okay!”

I told him to shush, as I didn’t want anyone to know I was over. He started laughing, thinking it was silly of me to be so discreet.

“Juan, are you home?” I heard a man yelp.

“Yeah, I’m in here!” he shouted back. “With a friend!”

I started sweating so hard and was so mortified that we weren’t alone.

We started having sex again, him even grunting really loudly. I was super insecure, as his host family could hear everything. I told him to finish it up.

When I started getting dressed, I headed out the door. Juan followed.

“Why don’t you tell your friend to come meet us!” they said, as I ran through the back door. “It’s not like we don’t know what ya’ll did in there!”

Three’s Company

One of my closest friends and I were out for a wild summer night. I’m not sure if it was the heat, the cocktails, or the fact that I was newly single and too eager to mingle, but somehow, we found ourselves at an orgy. We were both on Grindr and the same guy messaged us to join his merry group of horny cuties.

Neither one of us normally does this kind of thing, but we decided to say
fuck it” and join the party. All was well with some foreplay, until one guy showed up that the owner of the apartment really liked and we were all kicked out for them to have an intimate early am romp session.

To be honest, I was a bit relieved and ready to head home. However, my friend in a moment of people-pleasing suggested everyone head to his apartment to continue the party. He instantly regretted it, remembering his mom was visiting on his living room couch for the night.

He begged me to come even though I told him I was over it. During the long cab to the Bronx—yes, he lives all the way in the Bronx—he starts to fill in our new friends that there might be someone home. The long drive with this new information made the group start to question their decision. We got to his place, scurried into his tiny bedroom, and no one felt sexy.

It felt extremely awkward… especially when mom came knocking. He was mortified, I was hysterically laughing, and the boys exited in a huff. I wound up spending the night (ergh, early morning?) watching Bravo, giggling about the whole thing, and passing out. Neither one of us attended an orgy again.

Who peed in my wastebasket?

In 2011, when Hurricane Irene hit the East Coast everyone thought it was going to do some major damage in NYC. I was huddled up in my apartment alone all day but by 7 pm I had eaten all my emergency provisions (a box of pop tarts and a packet of bacon) and was bored out of my skull. I pushed through the torrents of rain to my favorite bar at the time, The Metropolitan.

Surprisingly, it was open and there were a handful of people there. As the storm raged outside we drank, danced, and agreed that if the world was ending we were glad to be in such fine company. A nice guy from my gym was there with his boyfriends. I had never met a throuple before and was intrigued. They invited me to go with them to a friend’s place.

We ran through the rain-swept streets, to a cute apartment near the waterfront. Inside there was a man and a woman. I assumed they were a couple but as the night went on and we drank more, he made it clear that he was interested in me. We had sex in his bed as the sky began to get light.

When I woke up much later I could tell from the light and the sounds outside, that it was past noon. I had to pee really bad! I pulled on my pants and went to the bathroom but someone was using it. I waited for what seemed forever but the door stayed closed.

I went back in to the room where last night’s host was still snoring away. I was in a state of panic when I saw the empty waste basket near his desk. I made my decision in a second and pissed into it for what felt like forever. It made a loud hissing sound. I kept looking towards the bed, worried he would wake up and be like, “What the hell are you doing? Were you raised by wolves?”

He didn’t stir. I quickly dressed and without looking back I bolted from the apartment. The rain had stopped. There were some downed trees branches and lots of rubbish blown about, but for all appearances it looked like NYC had survived yet another disaster. To this day I wonder if the guy from that night ever tells people about the weirdo who peed in his waste basket.

Adventurous and Abroad

A few years ago, I spent a few months living in Asia for a study abroad program. Working by day and visiting a variety of clubs by night. It wasn’t uncommon for me (being one of the few Caucasians and pretty good looking,IMO) to draw the eyes of some of the females who were also inhabiting the same club as me. One night I was lucky enough to hit it off really well with a girl and we started spending time together. Eventually, I asked her on a date which ended with us returning to my residence to do the dirty.

Right before we could start she asked me to grab a towel, which caught me slightly off guard as I was wearing a condom and I wasn’t sure what mess would really be created. However I grabbed a towel and handed it to her and she looked at me and said: “thanks, I’m on my period and don’t want to stain your sheets”. Mind you I’m staying in a shared hotel room with a friend on some white sheets. Needless to say, we went about having fun with our night and the towel did close to nothing to prevent blood from getting anywhere. Which wasn’t ideal but really didn’t bother me, I was just happy to be included.

Moving forward to the next day, I had a few great interactions as the fallout to my actions. The first was my roommate returning home around 8-9 a.m. and yelling “what the hell did you do?” as he caught sight of the blood-stained bed. The second being, seeing we were staying in a hotel room service came by to clean the room and without question, they replaced my sheets. However, the hotel manager must’ve contacted the staff running the study abroad program I was apart of.

All 25 students studying abroad including myself got a message along the lines “if anyone is ever hurt, please let us know”. Which started a conversation in the student group chat about who might be hurt and what that might be about, and me getting ousted to everyone about my sexual activity.

Sex Shop Newb

As a transgender male, I never had the experience of having sex “the normal way”. It was strictly oral or fingering. But, it wasn’t until my girlfriend and I were going on a trip that I decided to buy a strap on. I had an early shift the day I decided to buy one so, I went after work. I went to a place called Romantic Depot and after contemplating whether to go in or not for 5 minutes, I finally opened the door.

With my luck, I was the only one inside which made it even more intimidating. I was greeted by a very friendly woman who asked “What can I help you with today?” I was so nervous, I poured my heart out and said “So I’m transgender and I want to buy a strap on but I have no idea which one so can you help me?” She laughed and said okay and showed me everything in the store. She showed me the best harnesses and best dildos to start off with. She showed me one that was 9 inches and I quickly steered away from it. “That’s huge!” I said but she quickly said back to me “But everyone is trying to bust a nut right?” I laughed but still declined.

When we finally agreed on a size and harness I wanted, I bought it. After I left, I couldn’t believe I spent $80 on this. I pulled my phone out and called my girlfriend and without even saying hello I said “So, I bought it.” She laughed because she knew exactly what I bought. I asked her to come over after work because my parents were on vacation. I rushed home and I searched up YouTube videos on how to put on the harness because I was lost. When I finally figured it out, I put it in my drawer and waited for my girlfriend to get to my house. When she got there, we talked briefly and then she asked me “So, where is it?” I wearily said “In my drawer” She walked over to it and took it out and laughed because the strap on was white and I’m black. “It was the only one they had that wasn’t huge! I wasn’t trying to kill you.” She said it was fine. I put it on and I asked “So how do you do this?”

After being intensely frustrated for 5 minutes, I said “I’m just going to search this up online because I can’t be bothered” I quickly searched in “Sex positions with pictures” and showed them to her. “We can do this one maybe?” She laid down on her back and I tried to get on top of her and I yelled “Cramp!” My girlfriend laughs at me and says “You’re so old” This was a lot harder than I thought. Eventually, we finally got into it and it ended up being a really good experience despite the difficulties prior. Using a strap on is extremely tiring. You could definitely lose some weight using it. But, if I had to do it again, I wouldn’t change a thing.”

Umm… come again?

After moving back into the dorms early one semester, I decided I wanted to spice my night up. I want to say this was 2018, I came back to my dorm and had about two days before the rest of my suitemates came in. Suddenly, this guy hsst me up. After chatting for awhile, we decided to meet in my dorm. He was a muscular Nigerian guy and as we began to have great sex abruptly he says, “I’m going to get you pregnant.” A record scratch goes off in my brain. Wait a minute, I was mentally freaking out because, I’m a guy I don’t know if that was supposed to be a turn on or he was just caught up in the moment.

Michael Ealy

This is a story of an embarrassing sexual encounter, (but also about self-worth). There was this really hot six foot five light skin guy from Washington Heights who played basketball and resembled the actor Michael Ealy.

He had me just as shook as Michael Ealy’s role in color girls. I was up one late night really bored with nothing really to do so I decided to log into this app named Jack’d and this hidden profile with no profile picture hit me. I usually don’t even waste my time with hidden profiles just off of the simple fact is that I don’t have time to call Nevs & Max from Catfish.

Here I am ignoring Charles Darwin’s theory of natural selection. I know we have all heard the stories of people being kidnapped, raped, robbed, and blasé blasé end is also extra sketchy for people of the LGBT community because we really don’t have a safe space to meet not even on gay apps. After all, you hear stories all the time! Anywho.

I said all that to say I still ignored all of those signs just because I was simply bored and also it’s been a couple of months that I have been with anyone. I decided to just entertain this conversation to see where I would even go talking ain’t never hurt anybody right? I told him that I will no longer continue to talk to him even though he kept saying and insisting about how good-looking he was, he finally sent me a photo of what he looked like and asked me would I come over and cuddle. As I was battling if I should go or not, he messaged stating he would pay for my Uber.

So you know, I take a bath, I’m squeaky clean and hop into my waiting cab. I get to the address and am in awe…he looks just like the pictures. As I am still trying to get over the fact that he is not a catfish, we head up to the second floor where his bachelor pad awaits. He told me to get comfortable so I sat on his bed and he turned on the TV. Out of everything to watch, he picks The Walking Dead, which is a complete mood-killer. He begins to feel up on me, and as the mood begins to set he asks if I want music. Of course I say yes, as he turns on the music I expected some Marvin Gaye and Chardonnay, some Luther Vandross but “What A Time to Be Alive” by Drake and Future begins to fill the room.

As he began to pull out a condom from a drawer, I quickly came up with the first excuse I could think of. I told him that my grandmother needed me. I ran out of there, faster than you can say “Jumpman.”

The Doctor’s In

I am in my apartment on 5th avenue in New York City getting ready to head over to this man’s apartment for a hookup. I hop into my Uber and when I get there, this handsome man reveals himself from behind the door wearing a pair of scrubs. Immediately, he asks “Are you into some foreplay?” I respond saying “Of course! I’m always down!” It’s a given that, since he was wearing scrubs, it was going to be doctor related, I just didn’t know to what extent.

As I step in he reveals to me that he is actually a doctor in real life. I think, wow what a healthy way to get this out. Instead of with patients of course, I’m here to support him and play out his fantasy. He’s very sexy, muscular, and has dark hair. I won’t say I have a type but I was sold. We walk in after greetings and he says, “What brings you in today?” As he grabs me by the hips and lifts me onto his kitchen counter. Hesitating, because I’m not too familiar with roleplay, he questions “Oh your leg hurts?” And I respond, “Oh yeah it totally hurts.” “Let me see where it hurts.” the doctor says as he begins pushing around on my leg. I wait a second and then wince and cough pretending to be in pain. “Oh there! Oh my God let me see what is wrong.” he says eagerly. He continues to tough my leg, turning it around everything is very clinical. Eventually he comes to the conclusion that my leg is broken. I’m like, “Are you serious? It’s my leg.” He responds: “Yeah, I am serious. We’re definitely going to have to put you into a cast.”

He stands up and the next thing I know, he goes into his kitchen cabinet and gets the actual materials out to create a cast on my leg. He spends the next 15-minutes plastering my entire leg all the way above my knee. While he is casting up my leg, I am just so flabbergasted by the fact that this is happening to me and the cast has made me immobile. I honestly felt safe so after the cast is on when he says, “Why don’t you lie down, like relax a little?” I let him whisks me into the bedroom and where I lie down with this plastered cast on me for the next 30 minutes.It was ridiculous and hilarious, something that I’ve never done before. After we finish having sex that was satisfying for both of us, he takes me back to the kitchen. He takes out a pair of giant cast removal shears and removes the cast in its entirety. When it’s completely off my never-broken-to-begin-with leg, I plant a kiss on his cheek and he sends me on my way. Long story short, I never went back for another “doctors appointment.”

Come and Go

Okay, so let me preface this story with the fact that I didn’t have sex in a long time at this point — like, a long time. So, I finally got to hook up with this girl that I was seeing, and things got pretty intense. And before she could even touch me, I came in my pants. This happened not once, but twice during the day. It’s funny now though because me and that same girl have been together for about four years now.

Flatulent Flattery

One time, me and this guy were fooling around in bed. And then, without any warning, I fart. Loudly. We just sat in silence for a solid 30 seconds before bursting into laughter. But, we don’t see eachother anymore… maybe it was the fart that chased him off?